Protecting-Group-Free Syntheses of ent-Kaurane Diterpenoids: [3+2+1] Cycloaddition/Cycloalkenylation Approach

Jin Wang; Benke Hong; Dachao Hu; Yuichiro Kadonaga; Ruyao Tang; Xiaoguang Lei

doi:10.1021/jacs.9b13722

Protecting-Group-Free Syntheses of ent-Kaurane Diterpenoids: [3+2+1] Cycloaddition/Cycloalkenylation Approach

J Am Chem Soc. 2020 Feb 5;142(5):2238-2243. doi: 10.1021/jacs.9b13722. Epub 2020 Jan 27.

Authors

Jin Wang^{1

2}, Benke Hong^{1

2}, Dachao Hu^{1

2}, Yuichiro Kadonaga^{1

2}, Ruyao Tang^{1

2}, Xiaoguang Lei^{1

2

3}

Affiliations

¹ Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering , Peking University , Beijing 100871 , China.
² Department of Chemical Biology, Synthetic and Functional Biomolecules Center , Peking University , Beijing 100871 , China.
³ Peking-Tsinghua Center for Life Sciences , Peking University , Beijing 100871 , China.

PMID: 31968171
DOI: 10.1021/jacs.9b13722

Abstract

The Yu's Rh-catalyzed [3+2+1] cycloaddition followed by a Pd-mediated 5-endo cycloalkenylation is shown to be a general and powerful approach for efficient construction of the tetracyclic core structure of ent-kaurane diterpenoids. The utility of this strategy was further demonstrated by concise and protecting-group-free total syntheses of ent-1α-hydroxykauran-12-one, 12-oxo-9,11-dehydrokaurene, and 12α-hydroxy-9,11-dehydrokaurene.

Publication types

Research Support, Non-U.S. Gov't